31077-70-0

Usage

Uses

Used in Pharmaceutical Industry:
4-O-(2,6-Diamino-2,6-dideoxy-α-D-glucopyranosyl)-6-O-(α-D-glucopyranosyl)-2-deoxy-D-streptamine is used as an antibiotic for the treatment of bacterial infections. The modification of kanamycin B with a hydroxy group at the 3'' position may improve its pharmacological properties, such as increased efficacy, reduced toxicity, or enhanced stability.
Used in Research and Development:
In the field of research and development, 4-O-(2,6-Diamino-2,6-dideoxy-α-D-glucopyranosyl)-6-O-(α-D-glucopyranosyl)-2-deoxy-D-streptamine can be used as a starting material for the synthesis of novel aminoglycoside antibiotics or as a tool to study the structure-activity relationship of kanamycin and its derivatives.
Used in Drug Delivery Systems:
Similar to gallotannin, 4-O-(2,6-Diamino-2,6-dideoxy-α-D-glucopyranosyl)-6-O-(α-D-glucopyranosyl)-2-deoxy-D-streptamine may also benefit from novel drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes. These systems could include organic and metallic nanoparticles or other advanced drug delivery technologies.

InChI:InChI=1/C18H36N4O11/c19-2-6-9(24)11(26)8(22)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)12(27)10(25)7(3-23)31-18/h4-18,23-29H,1-3,19-22H2

Upstream product

• 4696-76-8 kananmycin B 
• 671809-10-2 1,3,2′,6′-tetraazidoneamine 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 671809-27-1 (2R,3S,4R,5R,6R)-5-Azido-2-azidomethyl-6-[(1R,2S,3S,4R,6S)-4,6-diazido-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4-diol 

Relevant academic research and scientific papers

Delineating the biosynthesis of gentamicin X2, the common precursor of the gentamicin C antibiotic complex

Gentamicin C complex is a mixture of aminoglycoside antibiotics used worldwide to treat severe Gram-negative bacterial infections. Despite its clinical importance, the enzymology of its biosynthetic pathway has remained obscure. We report here insights into the four enzyme-catalyzed steps that lead from the first-formed pseudotrisaccharide gentamicin A2 to gentamicin X2, the last common intermediate for all components of the C complex. We have used both targeted mutations of individual genes and reconstitution of portions of the pathway in vitro to show that the secondary alcohol function at C-3″ of A2 is first converted to an amine, catalyzed by the tandem operation of oxidoreductase GenD2 and transaminase GenS2. The amine is then specifically methylated by the S-adenosyl-l-methionine (SAM)-dependent N-methyltransferase GenN to form gentamicin A. Finally, C-methylation at C-4″ to form gentamicin X2 is catalyzed by the radical SAM-dependent and cobalamin-dependent enzyme GenD1.

Regioselective Glycosylation of Neamine Core: A Facile Entry to Kanamycin B Related Analogues

(Matrix presented) Introduction of a sugar unit at either the O5 or O6 position of various neamine derivatives in excellent selectivity and yields is described here. Application to the synthesis of kanamycin analogues is also highlighted.